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Phenothiazine → 5-Acryloyloxymethyl-oxazolidin-2-one

HRID 3072
Notes
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Reaction equation

HRID 3072 reaction equation
[OH:1][CH2:2][CH:3]1[O:7][C:6](=[O:8])[NH:5][CH2:4]1.C(N(CC)CC)C.C1C2NC3C(=CC=CC=3)SC=2C=CC=1.[C:30](Cl)(=[O:33])[CH:31]=[CH2:32]>O1CCCC1>[C:30]([O:1][CH2:2][CH:3]1[O:7][C:6](=[O:8])[NH:5][CH2:4]1)(=[O:33])[CH:31]=[CH2:32]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 7108PhenothiazineHCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 102907735-(Hydroxymethyl)oxazolidin-2-one

Product 1

HCID 189342305-Acryloyloxymethyl-oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 8028Tetrahydrofuran
Solvent

Procedure

105 g (0.90 mol.) of 5-hydroxymethyl-oxazolidin-2-one were placed into a one liter, three necked, round bottomed flask equipped with a paddle stirrer and thermometer. This was followed by 500 ml of tetrahydrofuran, 101 g (1.0 mol.) of triethylamine and 0.5 g of phenothiazine. Stirring was started as 90 g (1.0 mol.) of acryloyl chloride were added dropwise in such a way that the contents of the flask were maintained at 30° C. or less. When the addition was complete, the contents were stirred overnight at room temperature. The triethylamine hydrochloride was filtered and the solution was allowed to stand over NaHCO3 and Na2SO4. The solution was filtered, transferred to a one liter, round bottomed flask and placed on a rotoevaporator. The solution was concentrated by purging with a stream of air while rotating the flask. The resulting liquid was confirmed by 13C NMR to contain a mixture of the desired product and unreacted starting material.

Workup

  1. customround bottomed flask equipped with a paddle stirrer
  2. additionwere added dropwise in such a way that the contents of the flask
  3. temperaturewere maintained at 30° C. or less
  4. additionWhen the addition
  5. stirringthe contents were stirred overnight at room temperature
  6. filtrationThe triethylamine hydrochloride was filtered
  7. filtrationThe solution was filtered
  8. concentrationThe solution was concentrated
  9. customby purging with a stream of air
  10. additiona mixture of the desired product

Sources & evidence

ORD record
ord-77519deec78d44d89cdc131b10b54df8
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05733648

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes